The Best History Walks in Sydney City

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Published May 4th 2017

Step Back in Time

Family friendly history tour of Sydney (by City of Sydney)

Sydney's CBD has an array of attractions and events, topped by the NYE fireworks spectacular to entertain tourists and locals throughout each year. While millions of visitors enjoy these highlights, there are just as many historical hits for city explorers. Step through Sydney's history with one of these top 5 walks.

Whichever walk you choose, take your time to imagine horse-drawn carriages, ladies in elaborate petticoats and gentleman with top hats, but stay safe.

While you're unlikely to become lost or abandoned on these popular walks in the inner-city, watch for signposts and warning signs, avoid wandering into construction zones and don't get caught by speeding Ubers or taxis when you cross streets.

Each of these walks offers unique highlights, worthy of regular return trips as seasons change.

Tucked in the labyrinth of laneways in Sydney, there are landmarks charting the history of our city, often missed by all but the savviest local.

Begin in Phillip Lane, near the State Library, with sandstone gutters and cobblestones leading to the 1870s Chief Secretary's Building and the stylish 1930s Astor apartments.

In Customs House, find your bearings atop a model of the city, regularly updated to reflect the city's changing skyline, particularly at Barangaroo.

Macquarie Place Park features the anchor of the Sirius, flagship of the First Fleet, an obelisk inscribed with distances to key sites and the canopy of a Victorian-era drinking fountain.

Nearby is Reibey Place, named for a former horse thief who achieved incredible wealth as a businesswoman in the new colony and now features on our $20 note.

In Bulletin Place, the news and current affairs magazine, The Bulletin, was published, with contributors including Banjo Patterson and Henry Lawson, both queuing at the editor's office to receive their commissions.

At Angel Place, scan in all directions, with Romanesque buildings from the turn of the 20th century, the dazzling white AWA Tower rising skyward, the Edwardian Angel Hotel with ornate fixtures and the enthralling City Recital Hall surrounding you.

In the GPO, descend below the clock tower to see an Tank Stream exhibition, dedicated to the original water source flowing beneath your feet.

Over 100 plaques are dotted throughout Kings Cross, recording the lively events on these streets with artists, writers, entertainers and entrepreneurs and their adventures which still excite youthful imaginations.
Begin on the corner of Darlinghurst and Bayswater Rd, walking north until the El Alamein Fountain before returning south to Kings Cross Station.

The first plaque notes the exploits of two of the most infamous female criminals in Kings Cross history, Tilly Devine and Kate Leigh, dominating the underworld of prostitution, drugs and illegal gambling. Tilly was particularly vicious with razors, while Kate was quick to flash a pistol.

At nearby Minton House, despite interest by residental developers, the three storey 1920s office spaces are still open for rent, although perhaps now beyond the price range for the artists, writers and film makers that once worked here. If you need a space to work, ask for the office formerly rented to East Timor's Jose Ramos Horta.

Burt's Milk Bar, also from the 1920s, was perhaps Sydney's first and a popular hangout for local youth craving the jukebox, American snack/junk food and traditional milkshakes.

Kenneth Slessor's bohemian insights were written in the apartment on the corner, including the poem William St, beginning with the enticing lines,
"The red globe of light, the liquor green,
The pulsing arrows and the running fire
Spilt on the stones, go deeper than a stream;"

At the Woolworths Building, now housing Kings Cross Library, you could enjoy the classical melodies of our Sydney Symphony Orchestra, rehearsing during the 1950s.

Celebrate the theme of the next plaque, coffee and cake, at a Kings Cross local favourite, Vittorio Bianchi's Piccolo Bar.

William Dobell, the controversial and gifted artist and winner of the Archibald Prize in 1943, lived on the corner at Roslyn St as he helped establish the next generation of artists in the Cross, with works displayed in Clune Galleries.

Until the railway sliced through Newtown in the 1850s, the region was a rural escape with family estates.

Begin your walk at the train station which brought new people, ideas and colour to Newtown.

On your 2-hour walk along King and Wilson St with a few diversions, you'll cross Newtown Bridge, the site of communist protests and pastor's sermons in the early 1900s.

In Bedford St, the abandoned Hub Theatre hosted vaudeville acts, foreign and 'adult' cinema until the temptations of the internet drew patrons away.

In Australia St, the courthouse, opened in 1885, is still noisy with legal drama while the fire station's horse drawn trucks have been replaced with big red fire engines.

Tread lightly across Camperdown Memorial Rest Park, the former site of Camperdown Cemetery, with almost 18,000 people resting here since the mid-1800s.

Onto the spine of Newtown, King St, the busy retail strip unrecognisable as a former Indigenous track.

In Wilson St, the former home of the "Independent Order of Odd Fellows" and more recently, a gym for boxing greats, is now an apartment block.

Nearby in Georgina St, the faithful will celebrate the centenary of the synagogue in 2019 while the Trocodero echoes with laughter from patrons roller skating, playing billiards or sampling French champagne and oysters.

The apartments on O'Connell St were home to a recreation club with a shooting range on the rooftop. If you do hear gunshots, call for help and dart into Dendy, the cinema was a former emporium of millinery, boots and fancy goods spanning 10 acres.

Begin at the Basement, famous for local jazz talents including Benny Carter and Jackie Orszaczky before passing King St and the MLC Centre, where Lucifer's nightclub was rocking.

In the Strand Arcade, fashion and music blended during the 80s with performers scanning the racks for eye-watering fashions and outlandish hairstyles.

Event Cinemas has replaced our top glamour hall, the Trocadero, where Hollywood stars were entertained as chairs were tossed during an Elvis Costello concert in the nearby Regent.

The music still blares at the Metro, with musos from Placebo and the Dandy Warhols to Eskimo Joe and Alex Lloyd hitting the high notes.

On Goulburn St, Chequers, an exclusive nightspot in the 1960s, hosted Liza Minnelli and Frank Sinatra for a 'quiet' nightcap while the Mandarin and Goulburn Clubs were equally popular but slightly more infamous, with gambling and 24-hour entertainment.

Continue west on Goulburn St for the Civic where the Hoodoo Gurus and Mental as Anything strummed.

While the views of the harbour are captivating, look closely and you'll discover some surprising highlights. The majority of this walk spans from Circular Quay to Museum Train Stations with a few optional detours west toward Wynyard and Central and east through the Royal Botanic Gardens.

You won't need a life jacket as you learn the creative uses for water in Sydney, at engineering marvels, ornamental fountains, public conveniences, drinking places and pools.

The walk begins at Chinatown's Golden Water Mouth, blending water in a symbolically protective gum tree, decorated with 23ct. gold leaf. Sip from the granite bowls at Frazer Fountain, beside the Anzac Pool of Reflection, opened on the eve of World War II.

Water flows throughout Hyde Park, swirling at the Memorial Gates, with bronze crests and mosaic inlays and spouting at the art deco tourist hub, the Archibald Fountain, with Apollo ruling over a menagerie of mythical creatures.

Rub the golden snout of the Il Porcellino, the little pig, at Sydney Hospital on Elizabeth St for good luck before ducking under the swooping brolgas and black swans in Sydney Hospital's memorial fountain.

Resist the urge to make use of the P&O building fountain nicknamed the "urinal" before stepping beyond the bronze discs denoting the shoreline in 1788 at Circular Quay before we reclaimed land for development.

While the drinking fountain has been removed, receive spiritual sustenance from the Biblical inscriptions on the cast-iron canopy in Macquarie Place Park before splashing in the Tank Stream Fountain, celebrating the water source before it was covered with long tunnels.